C1 lounge rules - DEN

We have a trip to Denver next summer and am considering upgrading to the Venture X for lounge access. However, this is dependent on two factors.

1. Our flight out of Denver is a red eye (departure is almost 1am) and the rules state that guests may enter up to 3 hours before their departure time. The lounge closes at 9pm, 4 hours before our departure -- does that mean we will not be able to enter the lounge?
   
2. Venture X cardholders and Venture X Business primary cardholders enjoy unlimited complimentary access plus complimentary entry for 2 guests per visit to Capital One Lounge—and special pricing of $45 per visit for additional guests. We are traveling as a group of 4. Could the cardholder enter with two guests, leave, and then re-enter with the third guest to avoid paying the $45?